N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylthreonine → Fmoc-Thr-OTce

HRID 491282

Reaction equation

HRID 491282 reaction equation
[NH:1]([C:13]([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[C@H:2]([C:5]([O:7][CH2:8][C:9]([Cl:12])([Cl:11])[Cl:10])=[O:6])[CH2:3][OH:4].N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:31](C(O)=O)[C@@H](C)OC(C)(C)C>>[NH:1]([C:13]([O:15][CH2:16][CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:24]2[C:29]1=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:14])[C@H:2]([C:5]([O:7][CH2:8][C:9]([Cl:10])([Cl:11])[Cl:12])=[O:6])[C@@H:3]([CH3:31])[OH:4]

Participants

3

Reactant 2

HCID 6364643N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylthreonineHCID 10939458HCID 10939458, compound

Product 1

HCID 10994354Fmoc-Thr-OTceYield 68%

Procedure

According to the procedure used for the synthesis of Fmoc-Ser-OTce, Fmoc-Thr(OtBu)-OH (1 g, 2.5 mmol) provided Fmoc-Thr-OTce (0.81 g, 1.7 mmol, 68% overall yield for two steps).

Sources & evidence

ORD record
ord-ed601c4c828d4da998c62a8cb0ec6efe
Source dataset
uspto-grants-2009_05
Patent number
US07531506B2

Linked notes

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